Focus on Distressed Properties which is what we do in Hawaii which is a really tough market to do REI -- however, we make up our margin on forced equity to cash flow  properties.Don't give up just yet. 

I had a good paying position with a EV company that allowed me to build a good amount of reserves for investing.

There is plenty of equity in the property.

I originally bought it as a primary residence and intended on building up equity in it to then tap into for a HELOC to buy a second property.

I own two homes in Hawaii and not sure whether to sell or keep long term. 500k total equity.

If the latter, you can refinance in 6 months to a year (as the value of the property will likely go up with a renovation) and get the equity out to buy your next investment property.

They could do a better job matching same size, age, beds, <6 mo sales in the comp tool but at least it gives a list of area sales too plus last MLS listing's pictures (valuable).As far as pulling lists, yes PS has the most data types (liens, mortgage amount, equity) vs anyone else but its an ugly trueth in the data market place. 

Let's delve into the situation you've outlined:If your rental income exceeds the 27.5 years of depreciation and deductions, resulting in a positive net income, you are correct that this surplus becomes taxable income.

Some first time home buyer will overestimate their DIY skills and underestimate the scope of work and cost.While equity is a percentage (ideally 25%) rehab cost is a dollar amount that does not go down with lower priced properties.

And, at the moment, we’re not positioned to personally acquire more properties to manage unless it’s some creative, no money down, seller finance situation.